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Hawaii Sailing Charters

Big Island of Hawaii sailing charters often offer snorkeling as well as a sail.

There are 13 tours in this category with adult prices that range in price from $70.90 to $2700.00 Skip Directly to Tours.

"The Big Island" of Hawaii Sailing Charters

Many of the Big Island of Hawaii snorkeling cruises that take snorkel trips to various Big Island of Hawaii Snorkeling spots also have the capability to sail as well and hence offer a special double bonus for Big Island of Hawaii sailing enthusiasts.


Sailing conditions on the Big Island of Hawaii are generally determined by the existing wind patterns.


Generally speaking, the majority of the time the "trade winds" blow consistently from the north-east.


These winds provide excellent sailing conditions and are the best conditions for Big Island of Hawaii sailing charters.


Although the trade winds blow most of the time there is no question that some times of the year are better than others.


In the months of May through September the average percentage of days that blow from the "trades" averages about 90% of the time.


In the winter months the average falls to about 60% of the time and in the month of January the percentage actually falls to about 40%. The time of day also has an effect on the amount of wind that blows and obviously affects the quality of sailing Hawaii's sailing charters can provide their clients.


Mornings are generally fairly calm but as late morning comes the trade winds will pick up.


By mid afternoon the winds are usually at their strongest and these are the best times to catch a real stiff sail.


As sunset approaches the winds usually decrease and settle down to a gentle breeze which is ideal for a romantic sunset sail.


Pride of America Cruise Ship:

Many Big Island of Hawaii sailing charters are close enough to the arrival pier to allow you to take a taxi to meet them for a tour. Others can be best reached by renting a car from Tom Barefoot's Tours that will pick you up via shuttle at the pier. These Hawaii sailing boats are available when you arrive in Kona on the Wednesday of your cruise itinerary.

Do you still have questions about Sailing Charters?

    Look for this symbol in the tour descriptions below to indicate if it is Pride of America compatible.

    Sailing Charters Sorted by Specific Tour


    Sailing Charters Sorted by Company

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    (1 Review, 5 Stars)

    Sea Paradise

    3 Activity Options

    Snorkel - 50' Catamran

    Sea Paradise is a 50 foot sailing catamaran, the Hokuhele, which explores beautiful locations along the Kona coastline. Trips depart from Keauhou Bay heading down the coastline towards the historic marine preserve, Kealakekua Bay. Dolphins or even whales when in season will often become a major focal point of these trips. Evening tours are also available to see the amazing giant Manta Rays.
    More Info / Buy Now


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    (8 Reviews, 4.9 Stars)

    Fair Wind Charters

    2 Activity Options

    50' Sailing Catamaran, 55' Teknicraft Catamaran

    Well established as a tour boat company on the Kona Coast of the Big Island, Fair Winds Charters has two beautiful and distinctive boats that offer a complement of tours which include snorkel tours to Kealakekua Bay and evening Manta Ray excursions. Also included as a part of the day snorkels are SNUBA diving and the new sea rocket underwater propulsion vehicles.
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    (15 Reviews, 4.6 Stars)

    Kamanu Charters Inc.

    4 Activity Options

    36' Sailing Catamaran

    You'll enjoy "real sailing", snorkeling and whale watching on this trip with Kamanu Charters on their 36' custom designed sailing catamaran "Kamanu" to Pawai Bay. This area, located just north of Kona, is under State Fishery Management . The bay is within the Queen Liliuokalani Trust Land at Kaiwi Point and it is private. They also offer night manta ray snorkels.
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    Hawaii Nautical

    2 Activity Options

    Leid Back' Dinner Cruise, Snorkeling and Dolphins, Whale Watch off the leeward coastline,Oahu Scuba

    Hawaii Nautical offers a large variety of boat tours throughout the island of Oahu and on the Big Island of Hawaii. Snorkel tours and dolphin watches are offered in the mornings and the afternoons and in addition they offer sunset sails, dinner cruises, scuba and snuba options, whale watching in season and private charters.
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    Mauna Lani Sea Adventures

    1 Activity Option

    21' Power Catamaran, 50' Sailing Catamaran

    The beautiful Mauna Loa Resort in Waikoloa is the departure point for all the activities provided by the Mauna Lani Sea Adventures. Pristine snorkel adventures, scuba diving trips, sunset sails and whale watching trips in season are all available. The 55' Polynesian style catamaran 'Winona' carries intimate groups of passengers on tours along this gorgeous coastline.
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    Wahine Charters

    1 Activity Option

    Dolphin Excursions, Whale Watch Tour - Wahine Charters, Snorkeling and Manta Ray trips from Honokoha

    Wicked Wahine Charters operates a series of boat tours out of Kailua-Kona on the Big Island. Their 29' custom power vessel can easily traverse the 12 miles of coastline between Honokohau Harbor and the Captain Cook Monument while snorkeling and dolphin watching on the way, or it can take you out on a night time Manta Ray adventure or whale watching.
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    Recent Reviews


    Top Activities
    Customer Favorite Tours Based on Reviews

    So, how about sailing on the Big Island? We do sail there. We do have sailboats. We do have wind that can carry us along on the ocean. You may be surprised that we don't have as many strictly sailing-type ventures as you might think.

    If you're a sailing purist and you just want to get out on a boat, and you want to sail, and that's what you want to do, we can do that. We do have some charters that will do that with you. The majority, however, are going to be sailing charters that actually do something else, like snorkeling or whale watching, and then do some sailing as a part of the trip, kind of on the periphery as an additional thing.

    So, be careful which trips you choose, depending on what you're interested in doing. In all honesty, many people really enjoy sailing, but would want to include it with some snorkeling or some whale watching, that sort of thing, and then just have a portion of the day be sailing. But whichever category you fit in, we do have the capability of arranging this on the Big Island for you. Generally speaking, these are off the leeward coasts of Kona going up toward Waikoloa.

    If you have any questions about tours or activities in Hawaii, just give us a call, or check out tom-barefoot-dot-com. We're here to help.

    Sailing in Hawaii whether it be on a Hawaii sailboat charter, a Hawaii boat tour or a Hawaii yacht charter is simply a way of life in the islands. Keep in mind that the very first people to come to these islands came by virtue of a sail boat and so the sailing heritage runs deep in the waters surrounding Hawaii.

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    Kauai sailing, with its sailing boats offering snorkeling trips, snuba adventures, snorkeling from shore, family snorkeling activities and various other tours involving sailing off Kauai are among the most interesting tours that Kauai has to offer.

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    Let's get down to sailing basics. Oahu is an island that is surrounded by water and by wind. Sail boats are designed to catch the wind and sail on the water.

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    The stiff Maui's trade winds provide for great Maui sailing trips. If the notion of Maui sails intrigues you, you've come to the right spot. The Maui sailing climate and prevailing winds provide the best possible sailing environment.

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